Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

Sheng Jian Jia; Da Ming Du

doi:10.1016/j.cclet.2014.06.023

Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

Sheng Jian Jia
, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Enantioselective chlorination of β-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand-Cu(OAc)₂ complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric α-chlorination of β-keto amides. This study has highlighted that a simple chiral squaramide-oxazoline with cheap Cu(OAc)₂·H₂O complexes can catalyze this chlorination.

Original language	English
Pages (from-to)	1479-1484
Number of pages	6
Journal	Chinese Chemical Letters
Volume	25
Issue number	11
DOIs	https://doi.org/10.1016/j.cclet.2014.06.023
Publication status	Published - Nov 2014

Keywords

Asymmetric catalysis
Bisoxazoline
Chlorination
Squaramide
β-Keto esters

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10.1016/j.cclet.2014.06.023

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title = "Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand",

abstract = "Enantioselective chlorination of β-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand-Cu(OAc)2 complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric α-chlorination of β-keto amides. This study has highlighted that a simple chiral squaramide-oxazoline with cheap Cu(OAc)2·H2O complexes can catalyze this chlorination.",

keywords = "Asymmetric catalysis, Bisoxazoline, Chlorination, Squaramide, β-Keto esters",

author = "Jia, \{Sheng Jian\} and Du, \{Da Ming\}",

year = "2014",

month = nov,

doi = "10.1016/j.cclet.2014.06.023",

language = "English",

volume = "25",

pages = "1479--1484",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

number = "11",

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TY - JOUR

T1 - Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

AU - Jia, Sheng Jian

AU - Du, Da Ming

PY - 2014/11

Y1 - 2014/11

N2 - Enantioselective chlorination of β-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand-Cu(OAc)2 complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric α-chlorination of β-keto amides. This study has highlighted that a simple chiral squaramide-oxazoline with cheap Cu(OAc)2·H2O complexes can catalyze this chlorination.

AB - Enantioselective chlorination of β-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand-Cu(OAc)2 complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric α-chlorination of β-keto amides. This study has highlighted that a simple chiral squaramide-oxazoline with cheap Cu(OAc)2·H2O complexes can catalyze this chlorination.

KW - Asymmetric catalysis

KW - Bisoxazoline

KW - Chlorination

KW - Squaramide

KW - β-Keto esters

UR - https://www.scopus.com/pages/publications/84908398173

U2 - 10.1016/j.cclet.2014.06.023

DO - 10.1016/j.cclet.2014.06.023

M3 - Article

AN - SCOPUS:84908398173

SN - 1001-8417

VL - 25

SP - 1479

EP - 1484

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 11

ER -

Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

Abstract

Keywords

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